Place each cutlet between two sheets of plastic wrap and pound to an even ½-inch thickness. Season both sides with salt and pepper.
Set up three shallow dishes: flour in one; beaten eggs in another; panko, Parmesan, and garlic powder mixed in the third.
Dredge each cutlet in flour (shake off excess), dip in egg, then press into the panko mixture to coat both sides well.
Let the breaded cutlets rest 5–10 minutes, then lightly spray both sides with olive oil.
Preheat the air fryer to 400°F (200°C). Arrange cutlets in a single layer without overlapping (work in batches if needed). Air fry 10–12 minutes, flipping halfway, until golden and the internal temperature reaches 165°F (74°C).
While the chicken cooks, heat the olive oil in a skillet over medium heat. Sauté the shallot until soft, 2–3 minutes. Add the tomatoes, salt, and pepper; cook until they begin to burst, about 5 minutes. Pour in the red wine, scrape up any browned bits, and simmer 3–4 minutes. Stir in the basil off the heat.
Top each cutlet with a spoonful of sauce and serve with lemon wedges.